EP0741109A2 - Method and composition for enhancing biocidal activity - Google Patents
Method and composition for enhancing biocidal activity Download PDFInfo
- Publication number
- EP0741109A2 EP0741109A2 EP96301835A EP96301835A EP0741109A2 EP 0741109 A2 EP0741109 A2 EP 0741109A2 EP 96301835 A EP96301835 A EP 96301835A EP 96301835 A EP96301835 A EP 96301835A EP 0741109 A2 EP0741109 A2 EP 0741109A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- efficacy
- compound
- isothiazolinone
- dinonylsulfosuccinate
- surfactant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 CCC1C(*)C(*)(C(*)C(*)=CCC)C(*)C1 Chemical compound CCC1C(*)C(*)(C(*)C(*)=CCC)C(*)C1 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
Definitions
- surfactants which are able to inhibit the colonization of surfaces by inhibiting the overall growth of the organisms in the target environment. Most surfactants, regardless of class, show some inhibition of bacterial growth when used at concentrations high enough to impede surface colonization. In the water treatment industry, the most well known class of surfactants which impart a measure of colonization resistance to submerged surfaces are the cationic quaternary amine surfactants, which also function as biocides. However, even relatively mild nonionic surfactants can function in an analogous fashion. The concentration of nonionic surfactants necessary to mediate toxicity is substantially higher than for cationic surfactants, however.
- Surfactants have historically been added to biocide packages because they (1) help to maintain some actives in solution which may otherwise separate and (2) help relatively hydrophobic biocides to be more miscible in an aqueous environment. Surfactants have also been considered as enhancers of the efficacy of biocides against biofilm-associated organisms by increasing the accessibility of the biocide to its cellular target.
- the present invention refers to a method for enhancing the activity of biocides to control the growth of microbes in an aqueous system.
- the materials of the present invention have been previously used in areas such as fiber wetting in the textile industry.
- Figure 1 illustrates isothiazolinone efficacy enhancement by 12 ppm dinonylsulfosuccinate against planktonic P. pickettii .
- Figure 2 illustrates dinonylsulfosuccinate enhancement of isothiazolinone efficacy against planktonic P. pickettii , at varying concentrations of dinonylsulfosuccinate.
- Figure 3 illustrates the dinonylsulfosuccinate enhancement of 2 ppm isothiazolinone against sessile populations of P. pickettii .
- Figure 4 illustrates alkylsulfosuccinate alkyl chain length vs. reduction in viable count of planktonic P. pickettii at 48 ppm concentration of surfactant.
- Figure 5 illustrates alkylsulfosuccinate enhancement of 2-bromo-2-nitropropane-1,3-diol (BNPD) efficacy against planktonic P. pickettii .
- BNPD 2-bromo-2-nitropropane-1,3-diol
- the present invention relates to a method for enhancing the activity of a treatment including a biocidal compound to control the growth of microbes in an aqueous system, e.g., a cooling water, pulping or papermaking system, which comprises adding to the system an effective amount of an anionic alkylsulfosuccinate surfactant.
- a biocidal compound to control the growth of microbes in an aqueous system, e.g., a cooling water, pulping or papermaking system, which comprises adding to the system an effective amount of an anionic alkylsulfosuccinate surfactant.
- the method of the present invention allows for a decrease in the amount of biocidal compound added to the system, while maintaining the efficacy of the treatment.
- a more environmentally acceptable outcome is achieved, in that less biocidal material may be used while still achieving the same level of efficacy.
- the method of the present invention will allow for a decrease in the amount of biocide fed to a system, without decreasing the efficacy of a particular treatment protocol.
- the biocides tested in the present invention were an isothiazolinone (specifically, a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, sold as Kathon® 886F, available from Rohm and Haas Co.) and 2-bromo-2-nitropropane-1,3-diol, or BNPD (available from Boots Chemical, Pte.).
- the isothiazolinone compound is considered to be the preferred biocide active for the present invention, but the present invention is not limited to use of that biocide.
- the organism chosen for the initial studies was Pseudomonas pickettii , a bacterial species, although it is anticipated that the present invention will be effective against other microorganisms, e.g., fungi.
- the initial screening of the biocides with and without surfactant was carried out using 48 ppm (active) of surfactant, and the surfactants chosen for these experiments were the sulfosuccinates.
- the preferred sulfosuccinate, dinonylsulfosuccinate demonstrated a significant enhancement of the activity of BNPD.
- a surprisingly significant increase in the efficacy of the isothiazolinone compound (Kathon 886F) in the presence of dinonylsulfosuccinate is shown in Figure 1.
- Dose-response curves demonstrated that as little as 5 ppm (active) of the dinonylsulfosuccinate compound would enhance isothiazolinone efficacy, particularly at higher isothiazolinone concentrations.
- diisobutylsulfosuccinate (4) diisoamylsulfosuccinate (5); dihexylsulfosuccinate (6); dioctylsulfosuccinate (8); dinonylsulfosuccinate (9); and bistridecylsulfosuccinate (13).
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
- Bacterial attachment to surfaces in virtually any non-sterile aquatic environment is a well-established phenomenon. Industrial efforts to prevent colonization or to clean fouled surfaces amount to costly expenditures in a number of industrial sectors. Surfactants are regularly employed in water treatment programs as agents believed to play a role in the removal of organic masses from surfaces, in the enhancement of biocide efficacy or in the assistance in the water miscibility of various biocidal agents. Surfactants are also regularly used in the agrichemical business, particularly to enhance the action of herbicides. This is accomplished by using the surfactants to alter the surface behavior of the applied droplets, maximizing their interaction with the leaf surface.
- There are numerous examples of surfactants which are able to inhibit the colonization of surfaces by inhibiting the overall growth of the organisms in the target environment. Most surfactants, regardless of class, show some inhibition of bacterial growth when used at concentrations high enough to impede surface colonization. In the water treatment industry, the most well known class of surfactants which impart a measure of colonization resistance to submerged surfaces are the cationic quaternary amine surfactants, which also function as biocides. However, even relatively mild nonionic surfactants can function in an analogous fashion. The concentration of nonionic surfactants necessary to mediate toxicity is substantially higher than for cationic surfactants, however.
- Surfactants have historically been added to biocide packages because they (1) help to maintain some actives in solution which may otherwise separate and (2) help relatively hydrophobic biocides to be more miscible in an aqueous environment. Surfactants have also been considered as enhancers of the efficacy of biocides against biofilm-associated organisms by increasing the accessibility of the biocide to its cellular target.
- The present invention refers to a method for enhancing the activity of biocides to control the growth of microbes in an aqueous system. The materials of the present invention have been previously used in areas such as fiber wetting in the textile industry.
- Figure 1 illustrates isothiazolinone efficacy enhancement by 12 ppm dinonylsulfosuccinate against planktonic P. pickettii.
- Figure 2 illustrates dinonylsulfosuccinate enhancement of isothiazolinone efficacy against planktonic P. pickettii, at varying concentrations of dinonylsulfosuccinate.
- Figure 3 illustrates the dinonylsulfosuccinate enhancement of 2 ppm isothiazolinone against sessile populations of P. pickettii.
- Figure 4 illustrates alkylsulfosuccinate alkyl chain length vs. reduction in viable count of planktonic P. pickettii at 48 ppm concentration of surfactant.
- Figure 5 illustrates alkylsulfosuccinate enhancement of 2-bromo-2-nitropropane-1,3-diol (BNPD) efficacy against planktonic P. pickettii.
- The present invention relates to a method for enhancing the activity of a treatment including a biocidal compound to control the growth of microbes in an aqueous system, e.g., a cooling water, pulping or papermaking system, which comprises adding to the system an effective amount of an anionic alkylsulfosuccinate surfactant. The method of the present invention allows for a decrease in the amount of biocidal compound added to the system, while maintaining the efficacy of the treatment. Thus, a more environmentally acceptable outcome is achieved, in that less biocidal material may be used while still achieving the same level of efficacy.
- The method of the present invention will allow for a decrease in the amount of biocide fed to a system, without decreasing the efficacy of a particular treatment protocol.
- The biocides tested in the present invention were an isothiazolinone (specifically, a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, sold as Kathon® 886F, available from Rohm and Haas Co.) and 2-bromo-2-nitropropane-1,3-diol, or BNPD (available from Boots Chemical, Pte.). The isothiazolinone compound is considered to be the preferred biocide active for the present invention, but the present invention is not limited to use of that biocide. The organism chosen for the initial studies was Pseudomonas pickettii, a bacterial species, although it is anticipated that the present invention will be effective against other microorganisms, e.g., fungi. The initial screening of the biocides with and without surfactant was carried out using 48 ppm (active) of surfactant, and the surfactants chosen for these experiments were the sulfosuccinates.
- The preferred sulfosuccinate, dinonylsulfosuccinate, demonstrated a significant enhancement of the activity of BNPD. In addition, a surprisingly significant increase in the efficacy of the isothiazolinone compound (Kathon 886F) in the presence of dinonylsulfosuccinate is shown in Figure 1. Dose-response curves demonstrated that as little as 5 ppm (active) of the dinonylsulfosuccinate compound would enhance isothiazolinone efficacy, particularly at higher isothiazolinone concentrations. The data also demonstrate that a near maximal increase in efficacy may be attained with as little as 12 ppm (active) of the dinonylsulfosuccinate (Figure 2). This effect is seen as an enhancement of isothiazolinone activity, as the surfactant, alone, did not mediate significant toxicity upon the bacterial population.
- In order to further evaluate the effectiveness of the alkylsulfosuccinate and biocide against sessile populations, efficacy trials in a recirculation device were conducted. Colonization in the absence of any antimicrobial or surfactant was allowed to proceed for two days, followed by the removal of the majority of the bacterial culture. The culture was replaced with either fresh media and biocide (control) or media with the addition of the appropriate amount of biocide and surfactant. The addition of a dinonylsulfosuccinate to about 2 ppm of isothiazolinone compound (Kathon 886F) greatly reduced the number of viable bacteria which could be recovered from colonized surfaces relative to the corresponding control (isothiazolinone only) surfaces (Figure 3). Other studies demonstrated that in the absence of any antimicrobial there was not a loss of adherent bacteria from the surfaces over the same time period.
- The following classes of compounds were tested, the number in parentheses indicating the carbon chain length on each ester chain: diisobutylsulfosuccinate (4); diisoamylsulfosuccinate (5); dihexylsulfosuccinate (6); dioctylsulfosuccinate (8); dinonylsulfosuccinate (9); and bistridecylsulfosuccinate (13).
- In reference to Figure 4, note that the 8 carbon chain length diesters were nearly as effective as the 9 carbon chain length diester compounds. Note also the increased efficacy with increased side-chain length up to 9 carbons. When the side-chain has a 13-C alkyl group there appears to be a loss of efficacy.
- The concentrations of isothiazolinone compound (Kathon 886F) used throughout these experiments, particularly the ones where efficacy against P. pickettii was being examined, was quite high (about 5 ppm). This is a reflection of the relative resistance of this organism to the isothiazolinone compound. Similar experiments were conducted using P. aeruginosa in which similar results were obtained with significantly lower concentrations of isothiazolinone.
- The effect of the efficacy of BNPD in the presence of dinonylsulfosuccinate or the dioctylsulfosuccinate against bacterial populations was also examined. The results (Figure 5) indicate that there is a significant increase in the efficacy of BNPD in the presence of dinonylsulfosuccinate but not in the presence of dioctylsulfosuccinate.
- It is expected that amounts of the treatment of the present invention as low as from about 1-5 ppm may be effective. Furthermore, other aqueous systems such as metal working and oil and gas systems will also benefit from the present invention.
- While we have shown and described herein certain embodiments of the present invention, it is intended that there be covered as well any change or modification therein which may be made without departing from the spirit and scope of the invention.
Claims (8)
- A method for enhancing the activity of a treatment containing a biocidal compound to control the growth of microbes in an aqueous system which comprises adding to said system an effective amount of an alkylsulfosuccinate surfactant, said method allowing for a decrease in the amount of biocidal compound added to said system, while maintaining the efficacy of said treatment.
- A method as claimed in claim 1, wherein said alkylsulfosuccinate surfactant is a dinonylsulfosuccinate.
- A method as claimed in claim 1 or 2, wherein at least about 1 ppm of the alkylsulfosuccinate surfactant is added to the aqueous system.
- A method as claimed in any of one of the preceding claims, wherein said microbes comprise bacteria.
- A method as claimed in any one of the preceding claims, wherein said microbes comprise fungi.
- A method as claimed in any one of the preceding claims, wherein said biocidal compound comprises an isothiazolinone compound.
- A method as claimed in any one of the preceding claims, wherein said biocidal compound comprises a bromonitropropanediol compound.
- A method as claimed in any one of the preceding claims, wherein said aqueous system comprises(i) a cooling water system,(ii) a pulping or papermaking system,(iii) a metal working system,(iv) an oil and gas system.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/431,338 US5607597A (en) | 1995-04-28 | 1995-04-28 | Method for enhancing biocidal activity |
US431338 | 1995-04-28 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0741109A2 true EP0741109A2 (en) | 1996-11-06 |
EP0741109A3 EP0741109A3 (en) | 1996-11-20 |
EP0741109B1 EP0741109B1 (en) | 2001-05-23 |
Family
ID=23711481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP96301835A Expired - Lifetime EP0741109B1 (en) | 1995-04-28 | 1996-03-18 | Method for enhancing biocidal activity |
Country Status (8)
Country | Link |
---|---|
US (1) | US5607597A (en) |
EP (1) | EP0741109B1 (en) |
AT (1) | ATE201388T1 (en) |
CA (1) | CA2171235C (en) |
DE (1) | DE69612908T2 (en) |
ES (1) | ES2156613T3 (en) |
NO (1) | NO961550L (en) |
PT (1) | PT741109E (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0904252A1 (en) * | 1997-01-15 | 1999-03-31 | BetzDearborn Inc | Method for enhancing biocidal activity |
WO2001062091A1 (en) * | 2000-02-25 | 2001-08-30 | Betzdearborn Inc. | Method for enhancing biocidal activity |
WO2012130822A1 (en) * | 2011-03-28 | 2012-10-04 | Arch Chemicals Inc. | Wet state preservation of mineral slurries |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6110381A (en) * | 1996-04-19 | 2000-08-29 | Betzdearborn Inc. | Method and composition for inhibiting microbial adhesion on surfaces |
US6241898B1 (en) | 1996-04-19 | 2001-06-05 | Betzdearborn Inc. | Method for inhibiting microbial adhesion on surfaces |
GB9716350D0 (en) * | 1997-08-02 | 1997-10-08 | Eastman Kodak Co | A method of inhibiting microbial growth in an aqueous medium |
US6514458B1 (en) | 2000-02-25 | 2003-02-04 | Ge Betz, Inc. | Method for removing microbes from surfaces |
US6428654B1 (en) | 2000-04-05 | 2002-08-06 | Hercules Incorporated | Fungicidal method |
DE60124906T2 (en) | 2000-06-05 | 2007-05-24 | S.C. Johnson & Son, Inc., Racine | BIOZIDE CLEANING AGENTS |
US20030194445A1 (en) * | 2001-11-12 | 2003-10-16 | Kuhner Carla H. | Compositions and methods of use of peptides in combination with biocides and/or germicides |
WO2007044398A2 (en) * | 2005-10-05 | 2007-04-19 | Novus International Inc. | Anti-microbial paper products having a substituted 1,2-dihydroquinoline |
US20080142453A1 (en) * | 2006-12-13 | 2008-06-19 | Michael Joseph Unhoch | Biocidal composition and method for treating recirculating water systems |
US20080269337A1 (en) * | 2007-04-30 | 2008-10-30 | Breen Alexander W | Method for the enhancing biocidal activity |
US20090127210A1 (en) * | 2007-11-20 | 2009-05-21 | Swisher Anthony E | Method and apparatus for water remediation |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0007591A1 (en) * | 1978-08-01 | 1980-02-06 | Ciba-Geigy Ag | Stable medicinal solution on the basis of 2,6-diamino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine(trimethoprim) and a sulphonamide, process for preparing and using it |
JPS57209201A (en) * | 1981-06-16 | 1982-12-22 | Shinto Paint Co Ltd | Water-suspending slime control composition for paper making |
JPS58183606A (en) * | 1982-04-21 | 1983-10-26 | Kumiai Chem Ind Co Ltd | Nonmedical agent inimical to microbe and alga |
JPS6341405A (en) * | 1986-08-08 | 1988-02-22 | Sankyo Co Ltd | Microbicide |
JPS6348202A (en) * | 1986-08-13 | 1988-02-29 | Sankyo Co Ltd | Microbicidal composition |
EP0302701A2 (en) * | 1987-08-05 | 1989-02-08 | Rohm And Haas Company | Microbicidal microemulsion |
JPH06298603A (en) * | 1993-04-13 | 1994-10-25 | Takeda Chem Ind Ltd | Granular agrichemical |
Family Cites Families (5)
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CA709376A (en) * | 1965-05-11 | A. Girard Theodore | Process for the control of slime-forming and other microorganisms and compositions for use in said process | |
US3411983A (en) * | 1964-08-06 | 1968-11-19 | Tenneco Chem | Process for the control of slime-forming and other microorganisms with 2, 3, 6-trichloro-5-nitrophenyl compounds |
US3452034A (en) * | 1967-03-09 | 1969-06-24 | American Cyanamid Co | Substituted 2-(1,3,4-thiadiazol-2-yl)-4(5)-nitroimidazoles |
US4732905A (en) * | 1987-03-13 | 1988-03-22 | Betz Laboratories, Inc. | Biocidal compositions and use thereof containing a synergistic mixture of 2-bromo-2-nitropropane-1,3-diol and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one |
SE467667B (en) * | 1988-08-11 | 1992-08-24 | Grace W R & Co | PROCEDURES CONCERN REGULATION OF PRODUCTION CONTROLLING MICROBIOLOGICAL PROVISIONS ON PAPER MANUFACTURING EQUIPMENT |
-
1995
- 1995-04-28 US US08/431,338 patent/US5607597A/en not_active Expired - Lifetime
-
1996
- 1996-03-07 CA CA002171235A patent/CA2171235C/en not_active Expired - Fee Related
- 1996-03-18 DE DE69612908T patent/DE69612908T2/en not_active Expired - Fee Related
- 1996-03-18 EP EP96301835A patent/EP0741109B1/en not_active Expired - Lifetime
- 1996-03-18 AT AT96301835T patent/ATE201388T1/en not_active IP Right Cessation
- 1996-03-18 ES ES96301835T patent/ES2156613T3/en not_active Expired - Lifetime
- 1996-03-18 PT PT96301835T patent/PT741109E/en unknown
- 1996-04-19 NO NO961550A patent/NO961550L/en not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0007591A1 (en) * | 1978-08-01 | 1980-02-06 | Ciba-Geigy Ag | Stable medicinal solution on the basis of 2,6-diamino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine(trimethoprim) and a sulphonamide, process for preparing and using it |
JPS57209201A (en) * | 1981-06-16 | 1982-12-22 | Shinto Paint Co Ltd | Water-suspending slime control composition for paper making |
JPS58183606A (en) * | 1982-04-21 | 1983-10-26 | Kumiai Chem Ind Co Ltd | Nonmedical agent inimical to microbe and alga |
JPS6341405A (en) * | 1986-08-08 | 1988-02-22 | Sankyo Co Ltd | Microbicide |
JPS6348202A (en) * | 1986-08-13 | 1988-02-29 | Sankyo Co Ltd | Microbicidal composition |
EP0302701A2 (en) * | 1987-08-05 | 1989-02-08 | Rohm And Haas Company | Microbicidal microemulsion |
JPH06298603A (en) * | 1993-04-13 | 1994-10-25 | Takeda Chem Ind Ltd | Granular agrichemical |
Non-Patent Citations (5)
Title |
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PATENT ABSTRACTS OF JAPAN vol. 007, no. 061 (C-156), 15 March 1983 & JP-A-57 209201 (SHINTOU TORIYOU KK), 22 December 1982, * |
PATENT ABSTRACTS OF JAPAN vol. 008, no. 015 (C-206), 21 January 1984 & JP-A-58 183606 (KUMIAI KAGAKU KOGYO KK), 26 October 1983, * |
PATENT ABSTRACTS OF JAPAN vol. 012, no. 252 (C-512), 15 July 1988 & JP-A-63 041405 (SANKYO CO LTD), 22 February 1988, * |
PATENT ABSTRACTS OF JAPAN vol. 012, no. 263 (C-514), 22 July 1988 & JP-A-63 048202 (SANKYO CO LTD), 29 February 1988, * |
PATENT ABSTRACTS OF JAPAN vol. 94, no. 010 & JP-A-06 298603 (TAKEDA CHEM IND LTD), 25 October 1994, * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0904252A1 (en) * | 1997-01-15 | 1999-03-31 | BetzDearborn Inc | Method for enhancing biocidal activity |
EP0904252A4 (en) * | 1997-01-15 | 2000-09-06 | Betzdearborn Inc | Method for enhancing biocidal activity |
WO2001062091A1 (en) * | 2000-02-25 | 2001-08-30 | Betzdearborn Inc. | Method for enhancing biocidal activity |
WO2012130822A1 (en) * | 2011-03-28 | 2012-10-04 | Arch Chemicals Inc. | Wet state preservation of mineral slurries |
US8317912B2 (en) | 2011-03-28 | 2012-11-27 | Arch Chemicals, Inc. | Wet state preservation of mineral slurries |
CN103476253A (en) * | 2011-03-28 | 2013-12-25 | 奥麒化工有限公司 | Wet state preservation of mineral slurries |
AU2012234326B2 (en) * | 2011-03-28 | 2015-08-27 | Arch Chemicals Inc. | Wet state preservation of mineral slurries |
CN103476253B (en) * | 2011-03-28 | 2016-05-18 | 奥麒化工有限公司 | The hygrometric state of mineral slurries is preserved |
Also Published As
Publication number | Publication date |
---|---|
ATE201388T1 (en) | 2001-06-15 |
NO961550L (en) | 1996-10-29 |
CA2171235C (en) | 2007-04-03 |
EP0741109B1 (en) | 2001-05-23 |
PT741109E (en) | 2001-08-30 |
CA2171235A1 (en) | 1996-10-29 |
NO961550D0 (en) | 1996-04-19 |
US5607597A (en) | 1997-03-04 |
DE69612908D1 (en) | 2001-06-28 |
DE69612908T2 (en) | 2001-09-20 |
EP0741109A3 (en) | 1996-11-20 |
ES2156613T3 (en) | 2001-07-01 |
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